For Crowley Hauling, a lot of what we do involves dump trucks, so I had a good sense of how things worked. Founding the company felt like a natural way to diversify — an example of “Screw it, just do it!”
Over time, we’ve slowly built up to six dump trucks. I suspect we will get to 10+ over the next year or so.
My final business, Crowley Properties, is an umbrella company that represents my ownership in each of the short-term rental properties I co-own in New Orleans and Tampa.
There wasn’t really any “ah-ha” moment. I spotted the Airbnb opportunity and acted on it. This area still has a ton of opportunity.
Our business model is to create amazing common areas and outdoor spaces. This strategy has worked very well in both New Orleans and Tampa. I think it will work in most cities, and we plan on finding out! Here are a few pictures and links to a few of our properties:
Take us through the process of building the first version of your products.
For Crowley Holdings, the initial goal was to get our first sale. To start, I randomly submitted bids for government RFQs. I think I first submitted a contract for 10,000 cardboard boxes and then a contract for 500 leather jackets for the Air Force. I basically called around to get prices for whatever product the RFQ called for then marked it up and submitted it to the government.
Eventually, I zeroed in on aggregate. I submitted a bid for a contract for roughly 700 tons of limestone for an Air Force Base in Belle Chasse, LA. We didn’t win that one, but we started submitting more and more aggregate bids.
Eventually, we won our first one in 2017. That’s when Ihad my “oh shit” moment: I realized I actually had to deliver 2,500 tons of graded aggregate base for the U.S. National Park Service in the Carolina Sandhills.
“Damn, do I need to fly out there?” “What if something goes wrong?” “Should I be on site to manage the deliveries?” These were just a few of the immediate thoughts that came to my mind. The project went smoothly, and a business was born!
Since then, we’ve slowly built up to 6-7 employees. Our next venture is trying to break into heavy civil construction work. We will do work for the U.S. Army Corps of Engineers to rebuild levees and other earthwork — definitely moving up to the big leagues. To start, these will be $5-10 million per project, but ultimately, I think we can get to $50-100 million revenue per year.
For Crowley Haulings, the idea formed after I spoke with someone who owned dump trucks. He connected me with a sales rep, and I eventually negotiated and bought my first truck in mid-2020:
- I paid roughly $180,000
- Financed 100% of the truck
- Over a five-year payback period
- At a 5.5% interest rate
One huge benefit to buying dump trucks is that you can finance 100% of the truck and also depreciate 100% of the truck in the first year.
As long as you have a good infrastructure — and can keep the trucks busy and profitable — you can just match each year with how well you are doing in your other businesses to offset income taxes.
This is a good case study on how depreciation for tax purposes helps spur job growth. If you are looking at $200,000-$1 million in income, then you can just buy one to five dump trucks that year and depreciate them 100%. There is definitely risk here of course, but in theory, it could work that way.
For Crowley Properties, I started in 2012 with a business partner of mine (we still work together) by flipping a house in New Orleans. We bought our first house for $72,000, put sweat equity and about $50-60,000 into it, and sold it for $180,000. I think we ended up netting about $35-40,000 on it. But that was our first deal, and it worked!
We went on to flip five more houses. Eventually, we started holding our properties and renting them out. That decision led us to where we are now.
Describe the process of launching the business.
With all of my businesses and ventures, one process is constant: going through the reps. Once you go through the process once, you then adjust and it gets easier. Completing the second flip is much easier than the first. Buying and operating the second dump truck is much easier than the first. Winning the second government contract is way easier than the first.
So I would say my process is: just let it rip! Get it out there and tweak.
Since launch, what has worked to attract and retain customers?
This question mostly applies to Crowley Properties. To attract customers to stay at our properties, we focus on quality and value.
If you look at any of the property links you will see that we have:
- 5+ bedrooms: The more guests you can accommodate, the more the group can spread out the nightly cost ($1,000/night spread out over 10 guests is only $100/night — much cheaper than any quality hotel).
- 3+ bathrooms: If you have 10+ guests, you need to have a lot of bathrooms.
- Amazing outdoor and common areas: This is what grabs the customer and gets them excited.
- Professional photos: Pictures are what books a place. Everything should be perfect in the pictures, otherwise retake them.
- The details: Customer service, informative listings, and a spotless property are all essential.
How are you doing today and what does the future look like?
Business is good! Crowley Holdings and Crowley Properties are both profitable and growing. They more or less were always profitable from the jump.
Crowley Holdings will continue to grow organically. Currently, we operate around the country and have found a niche in sand and gravel supply contracts. In the future, I imagine we will grow to have a real presence in New Orleans — and Louisiana at large — as a legitimate construction company. We are able to shake things up a bit by bringing in tricks, techniques, and technology that aren’t common in the construction industry. In five years, I anticipate we can be a $50-100 million revenue business.
Crowley Properties continues to grow and be profitable. I am currently adding five to 10 units per year. We just started expanding into Tampa, Fla. We have two properties there, with a third in the works. I’m currently deciding if I should keep growing organically or whether I should go out and raise some cash and add 20-30+ units peryear. If anyone has advice here, I would love to hear it!
Crowley Hauling is a solid business. It will never be a hockey stick type of company. But it is a good way to diversify. I also could see pairing Crowley Hauling with Crowley Holdings.
Ultimately, I believe we’ll be able to win big levee or construction projects in New Orleans and run our dump trucks on the job. This way, we can double dip. I can see us getting to 10 dump trucks in the next year or two. Beyond these goals, I’m not sure if I want to take it to the next level — 20, 30, 40 dump trucks. It’s doable, but we will see.
Did you ever have an “oh shit” moment where you thought it wouldn’t work?
Honestly, not with my three core businesses. However, I have launched products or businesses that did not work, including:
- Playboy alarm clock app: My first product that I successfully launched to the app store. I spent around $5,000 on it and made maybe $500 on it.
- Down River Design: I took what I learned from the Playboy alarm clock app and launched a web and app development company. I built the alarm clock with a software development firm in India. So I did the same thing for clients. I made some money, but I could never turn the corner of getting enough business to hire or grow.
- ZAP DRD: I partnered with the India-based company, Zaptech Solutions, giving it the name ZAP (Zaptech) DRD (Down River Design). I had the same problem. This move helped, but the business still never became super profitable.
- Lead-Buddy: This lead generation business sort of worked but never turned the corner.
In addition to a few other ideas that never made it.
Through starting your businesses, have you learned anything particularly helpful or advantageous?
Your business will never be perfect. Often, you see people trying to make everything perfect before launching their business or product. Most businesses fail before they start because they never make it to market (I don’t have any stats to back this up, but I would be willing to wager it is correct). You need to get it out to market ASAP — asap and you can always tweak it.
What platform/tools do you use for your business?
Trello: What we use to organize thoughts and projects.
Clickup: Similar to Trello but with more automation features. I might move the Crowley Holdings team from Trello to Clickup. I have been pretty impressed with it.
Slack: A must-have tool to communicate with the team efficiently.
Macs: I was a longtime PC guy, but Apple finally won! Most of what I do is communicate with people. Being able to text and call from my computer helps out in a big way.
Virtual Champions: I think I’ve finally found a good virtual assistant. I’ve only used it for a short time, but I am already getting a lot of tasks out of backlog.
What have been the most influential books, podcasts, or other resources?
“The 4-Hour Workweek”: I read/listened to this book a few months ago, but I wish I had years ago. It all aligns well with my thinking: work smarter, not harder. Become efficient with your time. Use the free time this creates however you choose!
“My First Million” podcast: You all know it 🙂
“The Pitch” podcast: Slightly under the radar, it’s like the real “Shark Tank,” meaning the pitches are much closer to what it’s like in the real world.
Advice for other entrepreneurs who want to get started or are just starting out?
I’ll come back to my mottos: Screw it — just do it. Let it rip! You need to get out there and do it. If the business fails — well, you can apply what you learned to the next business.
Ask for advice. It took me too long to do this. Business is not that complicated. There are plenty of people out there who have done it before, who have made those same mistakes.
Also, most entrepreneurs and business owners actually like talking about their business and giving advice. Myself included! So never be afraid to network and ask questions.
You don’t need to work as hard as people like Gary Vee say. You don’t need to grind 20 hours/day for your business to work. Yes, it might take longer for it to be successful if you don’t but that doesn’t mean it’s going to fail.
Delegate. You need to delegate to grow — your business will never scale if you can’t learn to do this.
Are you looking to hire for certain positions right now?
I would be interested in a right-hand man/woman — someone I could teach all of my businesses, and eventually, have them handle a lot of the day-to-day things I handle. I don't know how or where to find someone like that. As such, I haven’t advertised or looked for this role yet.